With the understandings of the biological significance of tetracycline, this proposal is to design the first asymmetric total synthesis of a naturally occurring tetracycline, namely the parent tetracycline. It is the intention that the synthesis be convergent and efficient, stereoselective and stereospecific, versatile in utilizing the existing synthetic methodologies as well as potential new asymmetric methodologies, and useful for preparations of new tetracycline derivatives which are critical in providing solutions to the problems of bacterial-resistance to the existing tetracycline antibiotics.